Uploaded February 2026 | Updated September 2026, 2 weeks ago
This episode is presented by Mercury, the banking platform that makes this show possible. I can’t imagine trying to run my business without them. Learn more at mercury.com
Robert Mac is on the show today to teach us what he's learned from great comics like Jerry Seinfeld and Mitch Hedberg. Robert has been doing stand up for more than a decade, and I wanted to know what he's learned about how to be funny, how to tell a good story.
00:00:00 Introduction
00:02:03 The #1 rule of comedy
00:03:29 The incongruity technique
00:06:07 Changing scale and focus
00:06:36 Wordplay explained
00:09:53 Pattern recognition
00:12:13 Know your audience
00:14:59 Why winning isn't funny
00:17:48 Using misdirection
00:22:21 The bait and switch
00:24:51 How one word changes a joke
00:28:53 Why writing matters
00:31:28 Seinfeld's hidden technique
00:36:43 Misplaced focus
00:42:00 The rule of three
00:46:07 More wordplay
00:47:15 The power of short stories
00:52:46 The role of details and context
00:54:11 What it feels like to bomb
00:56:33 Robert's writing process
00:59:08 What comedy can't be taught
*About the host*
Hey! I’m David Perell and I’m a writer, teacher, and podcaster. I believe writing online is one of the biggest opportunities in the world today. For the first time in human history, everybody can freely share their ideas with a global audience. I seek to help as many people publish their writing online as possible.
*Follow me*
Apple: podcasts.apple.com/us/podcast/how-i-write/id1700171470
YouTube: youtube.com/@DavidPerellChannel
Spotify: open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv
X: https://x.com/david_perell
This episode is presented by Mercury, the banking platform that makes this show possible. I can’t imagine trying to run my business without them. Learn more at mercury.com
Robert Mac is on the show today to teach us what he's learned from great comics like Jerry Seinfeld and Mitch Hedberg. Robert has been doing stand up for more than a decade, and I wanted to know what he's learned about how to be funny, how to tell a good story.
00:00:00 Introduction
00:02:03 The #1 rule of comedy
00:03:29 The incongruity technique
00:06:07 Changing scale and focus
00:06:36 Wordplay explained
00:09:53 Pattern recognition
00:12:13 Know your audience
00:14:59 Why winning isn't funny
00:17:48 Using misdirection
00:22:21 The bait and switch
00:24:51 How one word changes a joke
00:28:53 Why writing matters
00:31:28 Seinfeld's hidden technique
00:36:43 Misplaced focus
00:42:00 The rule of three
00:46:07 More wordplay
00:47:15 The power of short stories
00:52:46 The role of details and context
00:54:11 What it feels like to bomb
00:56:33 Robert's writing process
00:59:08 What comedy can't be taught
*About the host*
Hey! I’m David Perell and I’m a writer, teacher, and podcaster. I believe writing online is one of the biggest opportunities in the world today. For the first time in human history, everybody can freely share their ideas with a global audience. I seek to help as many people publish their writing online as possible.
*Follow me*
Apple: podcasts.apple.com/us/podcast/how-i-write/id1700171470
YouTube: youtube.com/@DavidPerellChannel
Spotify: open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv
X: https://x.com/david_perell
